Transferring library from iPhone to MacBook Pro

After years of using iTunes on my old PC with my old iPod and now my iPhone, I finally have a MacBook Pro that I'd like to use for syncing iTunes with my phone. Despite Googling manically, I can't seem to find the best way to get all my music/videos/playlists etc. onto my Mac so I can start using iTunes on it. I've read about expod but is there an easier way? And will that restore my current playlists that I've painstakingly built up over the past six years? Any advice/thoughts would be most welcome, thanks.

When I plugged my iPhone into my new Mac it gave me the option to transfer all the purchased items on my phone to iTunes. It might be the same for you

That will probably work, but if these people are anything like me they have thousands of songs they transferred form CDs they bought prior to the advent of iTunes to their iPhones. I have maybe 10 songs I've paid for on iTunes and thousands from my CDs. It's those thousands that are a hassle.

There's also the issue of transferring the contacts and calendar to the Mac's address book and iCal.

I'm not in the boat, but my sister is. She got a new MBP for Xmas to replace her old powerbook G4. I'm pretty tech savvy and I couldn't figure out how to transfer things from a phone to the computer without buying software. It seems rather ridiculous for Apple to only allow the transfer to work one way. I think she's just gonna go to the genius bar to see if they can transfer everything from her phone to her new MBP.